Methyl (4'-hydroxy-1,1'-biphenyl-4-yl)acetate → (4'-{[2-(tert-Butoxycarbonyl)-3,6-dihydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetic acid

HRID 2076686Notes

Reaction equation

HRID 2076686 reaction equation
Br[CH2:2][C:3]1[C:15]([O:16]COC)=[CH:14][C:13]([C:20]([F:23])([F:22])[F:21])=[C:12]([O:24]COC)[C:4]=1[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[OH:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][C:42]([O:44]C)=[O:43])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1>>[C:8]([O:7][C:5]([C:4]1[C:12]([OH:24])=[C:13]([C:20]([F:22])([F:23])[F:21])[CH:14]=[C:15]([OH:16])[C:3]=1[CH2:2][O:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:36]=[CH:37][C:38]([CH2:41][C:42]([OH:44])=[O:43])=[CH:39][CH:40]=2)=[CH:33][CH:34]=1)=[O:6])([CH3:11])([CH3:9])[CH3:10]

Participants

3

Reactant 2

HCID 86088038Methyl (4'-hydroxy-1,1'-biphenyl-4-yl)acetateHCID 86617430Tert-butyl 2-(bromomethyl)-3,6-bis(methoxymethoxy)-5-(trifluoromethyl)benzoate

Product 1

HCID 86617429(4'-{[2-(tert-Butoxycarbonyl)-3,6-dihydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetic acidYield 17%

Procedure

According to a method similar to Example (40-2), Example (8-3) and Example (17-4), from tert-butyl 2-(bromomethyl)-3,6-bis(methoxymethoxy)-5-(trifluoromethyl)benzoate (154 mg, 0.34 mmol) obtained in Example (87-1) and methyl (4′-hydroxy-1,1′-biphenyl-4-yl)acetate (80 mg, 0.33 mmol) obtained in Example (6-2), the title compound was obtained (25 mg, three-step total yield: 17%).

Sources & evidence

ORD record
ord-a9c165e24cd14a7bbfa03916807ed460
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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